The Chicago Cubs are facing some big questions this offseason—like how to deal with the impending loss of their entire end-of-season starting rotation, a third of their bullpen, their starting catcher, and both corner outfielders.
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And they simultaneously have to worry about building something capable of upending the Milwaukee Brewers in the NL Central Division.
So, it can be forgiven if they just have to make way for some serious cuts in order to facilitate this upcoming soft rebuild.
One of those cuts is thought to be left fielder Ian Happ, who’s been a Cub his entire professional career, from draft day to the disappointing end of this 2026 season. The veteran is eligible for free agency and many are assuming that Chicago will let him walk.
Happ, himself, seems to think that also as he all but said his farewell to the city and to the organization after his last game. He even gave his final respects to the loyal Cubs fans, tossing a ball into the bleachers with $300 attached to it for “beer money” and sporting a heartfelt inscription of thanks.
“All I can say is that I love being a Cub,” Happ told reporters. “I’ve loved my time. I’ve loved the place, the people, Wrigley Field, the fanbase. And it’s been truly special. I don’t think there’s a better place in baseball to play.”
But maybe it’s not going to be “so long” after all.
Happ open to returning at a discount price?
Aug 25, 2026; Phoenix, Arizona, USA; Chicago Cubs outfielder Ian Happ tosses his bat after hitting a three run home run in the fourth inning against the Arizona Diamondbacks at Chase Field. Mandatory Credit: Mark J. Rebilas-Imagn Images
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Pat Ragazzo of Cubbies Crib is reporting that Happ would be open to taking a more Cubs-friendly deal if it meant being able to stay in Chicago:
“However, Happ’s time with the Cubs might not be coming to a close after all. A source familiar with Happ’s thinking told FanSided that they could see the outfielder taking a hometown discount in free agency to remain with the Cubs. As the source pointed out, Happ already signed a team-friendly three-year, $61 million extension to stay with the Cubs back in 2023. This could bode well for a chance at a reunion this offseason.”
Patrick Mooney and Sahadev Sharma of The Athletic, meanwhile, have opined that the Cubs may leave the door open for such a reunion:
“As polarizing as Happ is among the fanbase, bringing him back on a team-friendly deal isn’t entirely out of the question. He’s an above-average performer at the plate, a four-time Gold Glove winner and a valuable presence in the clubhouse.”
It makes sense
May 22, 2026; Chicago, Illinois, USA; Chicago Cubs left fielder Ian Happ (8) looks on from the dugout before a baseball game against the Houston Astros at Wrigley Field. Mandatory Credit: Kamil Krzaczynski-Imagn Images
It does make sense. Happ has firmly planted his roots in the Chicago community, forming the Happ Foundation charitable organization just last year, and just being a Chicagoan through and through. And, as noted, he’s already signed one extension three years ago to avoid free agency.
One could also argue that he’s not likely to get much more on the open market at 32 and after essentially finishing the year as a platoon player than what he got with the Cubs these last three seasons.
From the Cubs’ side of things, bringing Happ back would provide some stability and a temporary bridge until at least one of the organization’s top outfield prospects (Josiah Hartshorn, Kane Kepley, Ethan Conrad) is major league-ready.
With the loss of Seiya Suzuki looking more and more likely, the team would be in a really tough spot if they ended up without both of their corner outfielders.
Happ—with his elite defense and frustratingly streaky offense—being brought back is becoming more and more of a possibility.
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